Modern corporate enterprise organizations sometimes experience a “roving data protection” problem. In these organizations, employees can share files externally through emails, cloud applications such as DROPBOX and BOX, and removable media such as USB sticks. Each of these channels creates a potential vulnerability in which sensitive data can be lost or security can be compromised. Specifically, IT administrators have little or no control over data after the data leaves a corporate perimeter. These administrators may attempt to address some of these potential vulnerabilities by encrypting data to prevent unauthorized access to the data. Nevertheless, traditional systems for encrypting an organization's data may not be optimized along one or more dimensions, as discussed further below. The instant disclosure, therefore, identifies and addresses a need for improved systems and methods for encrypting files.